US3371109A - Carbamic acid esters of thiobisphenols - Google Patents
Carbamic acid esters of thiobisphenols Download PDFInfo
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- US3371109A US3371109A US376574A US37657464A US3371109A US 3371109 A US3371109 A US 3371109A US 376574 A US376574 A US 376574A US 37657464 A US37657464 A US 37657464A US 3371109 A US3371109 A US 3371109A
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- Prior art keywords
- thiobis
- carbamic acid
- grams
- employed
- acid esters
- Prior art date
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- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title description 6
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 title description 3
- -1 halophenyl isocyanate Chemical class 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- VTAQLGRULYHNQX-UHFFFAOYSA-N (3,4-dichlorophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=C(Cl)C(Cl)=C1 VTAQLGRULYHNQX-UHFFFAOYSA-N 0.000 description 2
- MFUVCHZWGSJKEQ-UHFFFAOYSA-N 3,4-dichlorphenylisocyanate Chemical compound ClC1=CC=C(N=C=O)C=C1Cl MFUVCHZWGSJKEQ-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
- 239000011369 resultant mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- TXPUFDMDZBCZLQ-UHFFFAOYSA-N (2,4-dichlorophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=C(Cl)C=C1Cl TXPUFDMDZBCZLQ-UHFFFAOYSA-N 0.000 description 1
- QNXVGKPQNAIJIF-UHFFFAOYSA-N (3,4,5-trichlorophenyl)carbamic acid Chemical compound OC(=O)NC1=CC(Cl)=C(Cl)C(Cl)=C1 QNXVGKPQNAIJIF-UHFFFAOYSA-N 0.000 description 1
- GLCIMEOOSALMQT-UHFFFAOYSA-N 1,2,3-trichloro-5-isocyanatobenzene Chemical compound ClC1=CC(N=C=O)=CC(Cl)=C1Cl GLCIMEOOSALMQT-UHFFFAOYSA-N 0.000 description 1
- HHIRBXHEYVDUAM-UHFFFAOYSA-N 1-chloro-3-isocyanatobenzene Chemical compound ClC1=CC=CC(N=C=O)=C1 HHIRBXHEYVDUAM-UHFFFAOYSA-N 0.000 description 1
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 1
- OLBJNSPBWLCTOT-UHFFFAOYSA-N 2,4-dichloro-1-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C(Cl)=C1 OLBJNSPBWLCTOT-UHFFFAOYSA-N 0.000 description 1
- FLBPYLKSSDOEOO-UHFFFAOYSA-N 3,4,6-trichloro-2-(2,3,5-trichloro-6-hydroxyphenyl)sulfanylphenol Chemical compound OC1=C(Cl)C=C(Cl)C(Cl)=C1SC1=C(O)C(Cl)=CC(Cl)=C1Cl FLBPYLKSSDOEOO-UHFFFAOYSA-N 0.000 description 1
- KYZSNVXYOQKZAK-UHFFFAOYSA-N 3,4-dibromophenol Chemical compound OC1=CC=C(Br)C(Br)=C1 KYZSNVXYOQKZAK-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- KYPYTERUKNKOLP-UHFFFAOYSA-N Tetrachlorobisphenol A Chemical compound C=1C(Cl)=C(O)C(Cl)=CC=1C(C)(C)C1=CC(Cl)=C(O)C(Cl)=C1 KYPYTERUKNKOLP-UHFFFAOYSA-N 0.000 description 1
- 229940052651 anticholinergic tertiary amines Drugs 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- CNFUKOAVELXSRS-UHFFFAOYSA-N chloro(phenyl)carbamic acid Chemical compound OC(=O)N(Cl)C1=CC=CC=C1 CNFUKOAVELXSRS-UHFFFAOYSA-N 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical class CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- MVXLHYKEKXUFFZ-UHFFFAOYSA-N phenyl n-(3,4-dichlorophenyl)carbamate Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(=O)OC1=CC=CC=C1 MVXLHYKEKXUFFZ-UHFFFAOYSA-N 0.000 description 1
- WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Chemical class C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/12—Radicals substituted by oxygen atoms
Definitions
- This invention relates to a novel class of carbamic acid esters of thiobisphenols. More particularly, this invention is concerned with a class of new organic compounds wherein a 2,2 thiobis(h-alophenol) is attached to one or two carbamic acid groups. Such materials have been found to possess useful and unexpected biological activity.
- novel compounds of this invention have the formula,
- R is selected from the group consisting of hydrogen and 0 -(")NHR
- R is selected from the group consisting of lower alkyl, phenyl, chlorophenyl of from 1 to 3 chlorine atoms and bromophenyl of from 1 to 3 bromine atoms
- X is selected from the class consisting of chlorine and bromine
- n is an integer from 1 to 3.
- the term lower alkyl connotes those alkyl groups, either straight or branch chain, having up to 4 carbon atoms.
- the carbamic acid esters of this invention can be prepared by reacting an alkyl, phenyl or halophenyl isocyanate with a 2,2 thiobis(halophenol). Such a reaction is illustrated by the following equation, which represents the use of equimolar quantities of both reactants:
- a tertiary amine In practicing the preparations of this invention, it is often preferred to employ a tertiary amine to catalyze or facilitate the progress of the reaction.
- ter tiary amines which can be employed are triethylamine, dimethylaniline, pyridine and the like. It is also preferred to carry out the reaction in the presence of an inert organic solvent. Suitable solvents include benzene, toluene, Xylene, the chlorinated benzenes, ethyl ether, propyl ether, tetrahydrofuran and the like.
- reaction temperatures employed in the preparation of the compounds of this invention will vary from room temperature to the reflux temperature of the reaction mixture.
- the specific temperature employed in any given case Will be primarily dependent upon the particular reactants used to produce the desired carbamic acid ester. It should be noted that, although the presence of both a tertiary amine and an inert organic solvent is preferred, neither of these materials is essential to the preparation of the compounds described herein.
- EXAMPLE 1 A suitable reaction vessel, equipped with a condenser, a stirrer, a thermometer and an additional funnel, is charged with a solution of 6.3 grams (0.11 mole) of methyl isocyanate in ml. of monochlorobenzene. The solution is stirred and heated to about 50 C. There is then added, dropwise over a period of V2 hour, 17.8 grams (0.05 mole) of 2,2 thiobis(4,6 dichlorophenol) in 100 ml. of monochlorobenzene. The resultant mixture is heated to about 100 C., after which it is cooled and filtered.
- EXAMPLE 4 A reaction vessel, as described in Example 1, is charged with 7.1 grams (0.02 mole) of 2,2-thibis(4,6-dichlor0- phenol) in 100 ml. of dry toluene. The solution is heated to 75 C. while 2 ml. of triethylamine and 20 ml. of dry ether are added. There is then added, dropWise over a period of 15 minutes, 3.8 grams (0.02 mole) of 3,4-dichlorophenyl isocyanate in 50 ml. of dry toluene. The resultant mixture is stirred for 2 hours at room temperature, and 50 ml. of Skellysolve B is added to enhance crystallization.
- EXAMPLE 5 Following the procedures set forth in Example 4, 3.1 grams of m-chlorophenyl isocyanate and 8.5 grams of 2, 2'-thiobis(3,4,6-trichlorophenol) are employed as the reactants. The product obtained is 2,4,5-trichloro-6-(2- hydroxy-3,5,6 trichlorophenylthio)phenyl m chlorocarbanilate.
- EXAMPLE 6 EXAMPLE 7 Following the procedures set forth in Example 6, 9.0 grams of p-chlorophenyl isocyanate is employed in place of the phenyl isocyanate. The product obtained is 2,2-thiobis(4,6-dichlorophenyl) bis (p-chlorocarbanilate).
- the products of the present invention are useful as microbiocides adapted to be employed for the control of bacterial and fungal organisms.
- 2,2-thiobis(4,6-dichlorophenyl) bis(3,4-dichlorocarbanilate) is found to be effective against Staphylococcus aureus at a dilution in excess of one part per million.
- Said compound is further found to be effective against both Aspergillus niger and Salmonella typhosa at a dilution in excess of one part per one hundred thousand.
- Similar activity against such organisms is also displayed by 2,4-dichloro-6-(3,5-dichloro-2-hydroxyphenylthio)phenyl 3,4-dichlorocarbanilate.
- R is selected from the group consisting of hydrogen and 0 l1 -cNHR QLD -Q C l n Clm Clm wherein m and n are each an integer from 1 to 3.
- n is an integer from 1 to 3
- Z is lower alkyl
Description
United States Patent 3,371,109 CARBAMIC ACID TESTERS 0F THIOBEPHENOLS Joseph Willard Baker, Kirkwood, and Ignatius Schumacher, Webster Groves, Mm, assignors to Monsanto Company, St. Louis, Mo., a corporation of Delaware No Drawing. Filed June 19, 1964, Ser. No. 376,574 9 Claims. (Cl. zen-471) ABSTRACT GF THE DISCLGSURE This disclosure covers certain carbamic acid esters of halogenated thiobisphenols. These esters have been found to be useful in the control of bacterial and fungal organisms.
This invention relates to a novel class of carbamic acid esters of thiobisphenols. More particularly, this invention is concerned with a class of new organic compounds wherein a 2,2 thiobis(h-alophenol) is attached to one or two carbamic acid groups. Such materials have been found to possess useful and unexpected biological activity.
The novel compounds of this invention have the formula,
wherein R is selected from the group consisting of hydrogen and 0 -(")NHR R is selected from the group consisting of lower alkyl, phenyl, chlorophenyl of from 1 to 3 chlorine atoms and bromophenyl of from 1 to 3 bromine atoms, X is selected from the class consisting of chlorine and bromine, and n is an integer from 1 to 3. As employed herein, the term lower alkyl connotes those alkyl groups, either straight or branch chain, having up to 4 carbon atoms.
The carbamic acid esters of this invention can be prepared by reacting an alkyl, phenyl or halophenyl isocyanate with a 2,2 thiobis(halophenol). Such a reaction is illustrated by the following equation, which represents the use of equimolar quantities of both reactants:
However, when the isocyanate and the thiobisphenol are employed in a molar ratio of about 2:1, the reaction is illustrated by the following equation:
In practicing the preparations of this invention, it is often preferred to employ a tertiary amine to catalyze or facilitate the progress of the reaction. Examples of ter tiary amines which can be employed are triethylamine, dimethylaniline, pyridine and the like. It is also preferred to carry out the reaction in the presence of an inert organic solvent. Suitable solvents include benzene, toluene, Xylene, the chlorinated benzenes, ethyl ether, propyl ether, tetrahydrofuran and the like.
The reaction temperatures employed in the preparation of the compounds of this invention will vary from room temperature to the reflux temperature of the reaction mixture. The specific temperature employed in any given case Will be primarily dependent upon the particular reactants used to produce the desired carbamic acid ester. It should be noted that, although the presence of both a tertiary amine and an inert organic solvent is preferred, neither of these materials is essential to the preparation of the compounds described herein.
The invention will be more fully understood by reference to the following examples, which are set forth herein for the purpose of illustration only and are not to be construed as limiting the scope of this invention in any manner.
EXAMPLE 1 A suitable reaction vessel, equipped with a condenser, a stirrer, a thermometer and an additional funnel, is charged with a solution of 6.3 grams (0.11 mole) of methyl isocyanate in ml. of monochlorobenzene. The solution is stirred and heated to about 50 C. There is then added, dropwise over a period of V2 hour, 17.8 grams (0.05 mole) of 2,2 thiobis(4,6 dichlorophenol) in 100 ml. of monochlorobenzene. The resultant mixture is heated to about 100 C., after which it is cooled and filtered. The filter cake is then washed with Skellylsolve B (an essentially n-heXane solvent having a boiling range of 70 C.) and dried. The product is recrystallized from acetone to yield 2,2 thiobis(4,6 dichlorophenyl) bis(rn-ethy1carbamate) as a white solid, M.P. 205 C. (decomp). Analysis shows 30.0% chlorine and 6.7% sulfur as against calculated values of 30.2% and 6.8%, respectively, for C H Cl N O S.
3 EXAMPLE 2 Following the procedures set forth in Example 1, 7.8 grams of ethyl isocyanate and 29.3 grams of 2,2-thiobis- (3,4-dibromophenol) are employed as the reactants. The product obtained is 2,2-thiobis(3,4-dibromophenyl) bis- (ethylcarbamate).
EXAMPLE 3 Following the procedures set forth in Example 1, 20.7 grams of 2,4-dichlorophenyl isocyanate and 17.8 grams of 2,2'-thiobis(3,4-dichlorophenol) are employed as the reactants. The product obtained is 2,2-thiobis(3,4-dichlorophenyl) bis(2,4-dichlorocarbanilate).
EXAMPLE 4 A reaction vessel, as described in Example 1, is charged with 7.1 grams (0.02 mole) of 2,2-thibis(4,6-dichlor0- phenol) in 100 ml. of dry toluene. The solution is heated to 75 C. while 2 ml. of triethylamine and 20 ml. of dry ether are added. There is then added, dropWise over a period of 15 minutes, 3.8 grams (0.02 mole) of 3,4-dichlorophenyl isocyanate in 50 ml. of dry toluene. The resultant mixture is stirred for 2 hours at room temperature, and 50 ml. of Skellysolve B is added to enhance crystallization. An ice-acetone bath is employed to complete precipitation. The product is recrystallized from Skellysolve B to yield 2,4-dicl1loro-6-(3,5 dichloro 2 hydroxyphenylthio)phenyl 3,4-dichlorocarbanilate as a White powder, MP. 199203 C.
EXAMPLE 5 Following the procedures set forth in Example 4, 3.1 grams of m-chlorophenyl isocyanate and 8.5 grams of 2, 2'-thiobis(3,4,6-trichlorophenol) are employed as the reactants. The product obtained is 2,4,5-trichloro-6-(2- hydroxy-3,5,6 trichlorophenylthio)phenyl m chlorocarbanilate.
EXAMPLE 6 EXAMPLE 7 Following the procedures set forth in Example 6, 9.0 grams of p-chlorophenyl isocyanate is employed in place of the phenyl isocyanate. The product obtained is 2,2-thiobis(4,6-dichlorophenyl) bis (p-chlorocarbanilate).
EXAMPLE 8 Following the procedures set forth in Example 6, 9.8 grams of 3,4-dichlorophenyl isocyanate is employed in place of the phenyl isocyanate. Upon recrystallization from acetonitrile, the product obtained is 2,2-thiobis(4,6-
' dichlorophenyl) bis(3,4-dichlorocarbanilate).
EXAMPLE 9 Following the procedures set forth in Example 6, 7.1 grams of 2,2thiobis(p-chlorophenol) and 12.3 grams of 3,4,5-trichlorophenyl isocyanate are employed as the reactants. The product obtained is 2,2-thiobis(p-chlorophenyl) bis(3,4,5-trichlorocarbanilate).
As stated above, the products of the present invention are useful as microbiocides adapted to be employed for the control of bacterial and fungal organisms. In representative tests, 2,2-thiobis(4,6-dichlorophenyl) bis(3,4-dichlorocarbanilate) is found to be effective against Staphylococcus aureus at a dilution in excess of one part per million. Said compound is further found to be effective against both Aspergillus niger and Salmonella typhosa at a dilution in excess of one part per one hundred thousand. Similar activity against such organisms is also displayed by 2,4-dichloro-6-(3,5-dichloro-2-hydroxyphenylthio)phenyl 3,4-dichlorocarbanilate.
While the invention has been described herein with regard to certain specific embodiments, it is not so limited. It is to be understood that variations and modifications thereof may be made by those skilled in the art without departing from the spirit and scope of the invention.
The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:
1. A compound of the formula,
wherein R is selected from the group consisting of hydrogen and 0 l1 -cNHR QLD -Q C l n Clm Clm wherein m and n are each an integer from 1 to 3.
3. A compound of the formula,
Cl (l) Clu 6:0 =0 I vH s11 l l wherein n is an integer from 1 to 3, and Z is lower alkyl.
4. A compound of the formula,
wherein n is an integer from 1 to 3, and Z is lower alkyl.
5. 2,2 thiobis(4,6 dichlorophenyl) bis(methylcarbamate).
phenyl 3 6. 2,2'-dich1oro-6-(3,5-dichloro-2 hydroxyphenylthio) ,4-dichlorocarbanilate.
7. 2,2-thiobis(4,6-dichlorophenyl) dicarbanilate.
ate)
9. 2,2 banilate) 8. 2,2-thiobis(4,6-dich1oropheny1) bis(p-chlorocarbanil- -thiobis(4,6-dichloroph-enyl) bis(3,4-dichlorocar- References Cited 5 LORRAINE A. WEINBERGER, Primary Examiner.
L. A. THAXTON, Assistant Examiner.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US376574A US3371109A (en) | 1964-06-19 | 1964-06-19 | Carbamic acid esters of thiobisphenols |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US376574A US3371109A (en) | 1964-06-19 | 1964-06-19 | Carbamic acid esters of thiobisphenols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3371109A true US3371109A (en) | 1968-02-27 |
Family
ID=23485554
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US376574A Expired - Lifetime US3371109A (en) | 1964-06-19 | 1964-06-19 | Carbamic acid esters of thiobisphenols |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3371109A (en) |
-
1964
- 1964-06-19 US US376574A patent/US3371109A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| None * |
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